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Thinking about how on and in are used:

we

go on vacation but don't go in vacation
speak on a topic but don't speak in a topic
think on it, but don't think in it

and we

fall in love, but not, fall on love
drive in a car, but not, drive on a car
speak in a language, but not, speak on a language

but we also :

fly on a plane and fly in a plane
ride on a bus and ride in a bus
sit on a chair and sit in a chair

On usually refers to being in contact with the surface of something, and in usually refers to being surrounded by something and so would be mutually exclusive, however the last three examples contradict this.

Except through repeated usage, is there a way to anticipate what the exceptions might be?

  • 2
    This sort of "on vs. in" issue has been done to death in several languages already... – Nihilist_Frost Dec 16 '15 at 17:10
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On usually refers to being in contact with the surface of something, and in usually refers to being surrounded by something and so would be mutually exclusive

Not really.

When you ride a mass-transit vehicle, you can stand up in it (at least when it's not moving). So on makes sense here. Especially buses - some might have standing room only. You will both be on and in the bus.

The same thing with a chair - a chair with armrests and a high back will surround you on all sides, but you are also atop the seat, so both in and on apply, depending on the type of chair. You wouldn't be in a barstool, but you'd definitely be in a recliner.

Except through repeated usage, is there a way to anticipate what the exceptions might be?

Not really. The "right" preposition with certain verbs and categories of nouns - especially certain nouns that don't refer to physical objects - is effectively arbitrary and needs to just be learned.

Speaking in French is a great example. You can invent situations to help you remember - perhaps a person who isn't familiar with a foreign language feels "surrounded" by the words in some sense.

Some hints and patterns:

  • An authority figure can put you on various states of freedom/grace - on vacation, on leave, on notice, on punishment, on administrative leave, etc.

  • Topics of conversation or meaning are something one is on.

  • Emotional states are something one is in - in love, in sadness, in madness, in good spirits, in ecstasy.

  • As I think has been mentioned before on ELL, vehicles are a little strange in that you're on a bicycle or motorcycle, in a car, but on a bus, ship, or airplane. – stangdon Dec 16 '15 at 17:00
  • @stangdon, you are correct in/on does get asked from time to time, however, the real part of the question is about ways to approach this, which usually does't get asked, but hopefully will be beneficial for ell'ers – Peter Dec 17 '15 at 13:11
  • What about "It is on the inside"? You don't hear people saying "It is in the inside" even though it would make more sense. – Jack Giffin May 20 '18 at 23:45
  • If you mean touching an inside surface, on the inside is fine. In the inside isn't used because you can just say inside. – LawrenceC May 21 '18 at 2:26
  • Arbitrary? Then, even native speakers can't expect which preposition would be well collocated with a word in some fixed expressions they happen to meet? If really so, how come they're even easily able to find out an error or awkwardness in a fixed expression miswritten by someone they face at first time? Do even they have to learn them one by one, as well as non-native speakers do? Can't they creat a new idiomatic expression naturally? – SinK Jan 10 at 0:16
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The preposition on is the most difficult of all English prepositions. The Longman Dictionary DCE distinguishes 30 uses in the entry "on, preposition". There is no handy rule for "on" and "in".

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You will remember each of them once you have used it a few time in different context.

Try to make a few examples on your own:

  • I am on vacation
  • He was on vacation last month.

Use it a few times in real-life context and it will pop up automatically next time you need to use it.

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